Sorry as this may be an easy question, but is there a way to set the
breakpoint to occur in every instance of a loop? It seems like the debugger
will stop once or twice and then finish the next 200 loops on its own.

Thanks

I never saw this behavior. Breakpoints always stop processing unless
following conditions:

a) An exception or "break" is putting you out of the loop
b) You have a conditional breakpoint (yes, you can customize "when
conditions" for your breakpoint.

To know if you have an exception not caugh by creating a "Exception
Breakpoint" (Ctrl+Shit+F8, then instead of "Class" breakpoint, select
"Exception") and fill the other options in the window.
You know that you have conditional breakpoint if it seems a "tetris L"
block instead of a square block.